Methanol → 2-[2-[(4-Chlorophenyl)sulfonylamino]indan-5-yl]ethanol

HRID 1086523Notes

Reaction equation

HRID 1086523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][C:22](O)=[O:23])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][CH2:22][OH:23])[CH:18]=3)[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 163920SX-AB 1316 SE

Product 1

HCID 151244462-[2-[(4-Chlorophenyl)sulfonylamino]indan-5-yl]ethanolYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2-[(4-Chlorophenyl)sulfonylamino]indan-5-yl]acetic acid (600 mg) is dissolved in tetrahydrofuran (20 ml) and thereto is added dropwise 7.8 M borane-1,4-oxathiane complex (1 ml). The mixture is stirred at room temperature for one hour and thereto is added methanol to terminate the reaction, and then, the solvent is distilled off under reduced pressure. The residue is dissolved in ethyl acetate and washed with aqueous sodium hydrogen carbonate solution and saline solution, dried and then distilled under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform) to give 2-[2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]ethanol (542 mg) as colorless crystals.

Workup

  1. additionis added dropwise 7.8 M borane-1,4-oxathiane complex (1 ml)
  2. customto terminate
  3. customthe reaction
  4. distillationthe solvent is distilled off under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with aqueous sodium hydrogen carbonate solution and saline solution
  7. customdried
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent, chloroform)

Sources & evidence

ORD record
ord-a430e7c2358a47ada0a927e39667b3f1
Source dataset
uspto-grants-1991_07
Patent number
US05030652

Reaction notes

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